Xingang Zhang, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, PR China

Short biography: Xingang Zhang obtained his BSc degree in 1998 from Sichuan University (China) and his Ph.D. in 2003 at the Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at the University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008 and became a research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology. He received the National Science Fund for Distinguished Young Scholars (2014), the RSC Fluorine Chemistry Prize (2015), the Chinese Chemical Society (CCS)-Royal Society of Chemistry (RSC) Young Chemist Award (2015), the CCS Wei-Yuan Huang Fluorine Chemistry Prize (2021), and the First Prize of the Shanghai Natural Science Award (2023).

Metal Difluorocarbene-Involved Catalytic Coupling

Xingang Zhang

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

345 Lingling Road, Shanghai 200032, China

e-mail: xgzhang@sioc.ac.cn

Keywords:organofluorine chemistry, metal difluorocarbene, catalytic coupling

Difluorocarbene is a highly reactive intermediate with a singlet ground state and is widely used in the synthesis of fluoropolymers, such as Teflon. Owing to its ability to form two chemical bonds, compared with fluorine-containing carbocations, carbanions, and free radical intermediates, difluorocarbene is capable of expanding the chemical space and efficiently creating novel organofluorine molecules. However, the high reactivity of difluorocarbene limits its reaction types and makes it difficult to apply in controllable organic synthesis. Theoretically, coordination of transition metals with difluorocarbene would alter the electron density distribution of difluorocarbene, thereby providing a possibility for modulating its reactivity. However, the transition metal difluorocarbene complexes isolated so far lack catalytic reactivity, and catalytic reactions involving metal difluorocarbenes pose a long-standing challenge. In 2015, we discovered the first catalytic coupling reaction involving a metal difluorocarbene.[1] This presentation will mainly introduce the latest progress in palladium and copper difluorocarbene chemistry.[2-7]

References

[1]Feng, Z.; Min, Q.-Q.; Zhang, X. Org. Lett. 2016, 18, 44-47.

[2] Feng, Z.; Min, Q.-Q.; Fu, X.-P.; An, L.; Zhang, X. Nat. Chem. 2017, 9, 918-923.

[3] Fu, X.-P.; Xue, X.-S.; Zhang, X.-Y.; Zhang, S.; Guo, Y.-L.; Len, X.; Houk, K. N.; Zhang, X. Nat. Chem. 2019, 11, 948-956.

[4] Zhang, X.-Y.; Sun, S.-P.; Sang, Y.-Q.; Xue, X.-S.; Min, Q.-Q.; Zhang, X. Angew. Chem. Int. Ed. 2023, 62, e202306501.

[5] Zeng, X.; Li, Y.; Min, Q.-Q.; Xue, X.-S.; Zhang, X. Nat. Chem. 2023, 15, 1064-1073.

[6] Zeng, X.; Yang, J.; Deng, W.; Feng, X.-T.; Zhao, H.-Y.; Wei, L.; Xue, X.-S.; Zhang, X. J. Am. Chem. Soc. 2024, 146, 16902-16911.

[7] Sun, S.-P.; Mu, T.; Zhang, X.-Y.; Fu, X.-P.; Zhao, H.-Y.; Zhang, Y.; Xue, X.-S.; Zhang, X. J. Am. Chem. Soc. 2025, 147, 38897-38906.